The Oral History of Okayplayer

The birth of the hip-hop website that started it all.

It’s hard to believe now, considering the horde of followers he’s amassed on Twitter (2.4 million strong and growing), but when the Internet first started popping off, Ahmir “Questlove” Thompson thought the revolution would be televised. Yes, if it wasn’t for a headstrong, witty, University of Pennsylvania student named Angela Nissel, Questo—the most famous drummer in the world and the most visible member of The Roots—might have stuck with WebTV and would never have gone on to found Okayplayer. And that would have been a shame because the site basically laid the foundation for most modern music blogs and shaped the way we discuss rap on the Internet.

Today OKP is based in NYC, and has expanded into a record label that produces live events. The site now boasts a tab called LNWJF that houses videos from The Roots’ performances on NBC’s Late Night With Jimmy Fallon, and affiliated specialist sites like the Revivalist for jazz, OkayAfrica for African music, the reggae site LargeUp, and Okayfuture, the newly launched site for electronic with hip-hop and soul aesthetics. There’s no denying it—Okayplayer is kinda major. But what we’re about to do right here is go back—all the way back.

Like most startups, Okayplayer began humbly—in Questlove’s Philadelphia bedroom, to be specific. In the beginning Okayplayer had no particular mission beyond chronicling the everyday dealings of all things The Roots. The site expanded to create lanes for various associated acts—of which there were many. But there were no advertisers and no suggestion of a road to profitability. This was a labor of love that grew into one of the most influential websites ever created. The web crew, like the band, was small, consisting of Questo, two programmers named Doug Muir and Shawn Gee, and, Angela, the “web mistress” and de facto editor, who birthed the site’s identity and distinctively irreverent voice.

Launched in 1999—four years before MySpace, five years before Facebook, and seven years before Twitter—Okayplayer was one of the first places where fans could interact directly with artists without a PR filter. The thrill of real-time interaction proved to be a powerful draw. In addition to its daily blog updates, the most popular part of Okayplayer, inspiring the love and ire of rappers and singers far and near, were the message boards. They attracted a motley crew of informed, sharp, and, at times hilarious hip-hop heads who would spit the most acrid of vitriol when provoked (often cloaked in a patina of positivity and “consciousness”). It didn’t matter if it was a fellow message board member or a rapper whose video had just graced Rap City—anybody could get it.

The web is now littered with music sites—some of which boast larger followings, more pageviews, and even bigger name backers. But none has had the formative impact that Okayplayer exerted on the culture. Think of it this way: Besides Reddit, what other site attracted a readership that feels enough like kin to have a yearly meet-up? But how did this site that angered Tweli Kweli enough to name drop it on song come to be? We let the people who were there from jump tell the story in their own words.

THE BEDROOM

Questlove: After high school, I couldn’t afford to go to Juilliard. At the time, I took off a year and a half to work at an insurance company that was paying significant money so I could save for college. This was back in ’89 / ’90. By that point, I had met my partner Angela Nissel who was a creative writing major at the high school I had just graduated from [Philadelphia High School for the Creative and Performing Arts]. We maintained an on-and-off friendship in that time period. She went to University of Pennsylvania. I would see her during The Roots’ struggling days.

Black people discovering technology is such a truly hilarious, albeit primitive, experience to observe. I was one of the suckers that purchased WebTV, which basically lets you surf on the Internet via your television. The same way that Angela wanted to smack me on the back of the head for not having a computer is the same way I’m trying to smack cats now—like half the cats that you see on Twitter now.

Black people discovering technology is such a truly hilarious, albeit primitive, experience to observe. —Questlove

By this point it’s 1997/1998—and surfing the “super information highway,” I would often go to the pages of bands that we toured with and bands that I liked and the only messages on their web sites were a weekly message to their fans. You know, I went to the Fugees page and it wasn’t even halfway updated from The Score. The only information I got that I didn’t know from reading magazines was Q-Tip’s spaghetti and clam recipe on the Tribe Called Quest page.

The first time I ever saw a chat-room board, it was Michael Stipe and Courtney Love fans having a debate about Roxy Music. I was fascinated. And I was like, “Wait a minute: Courtney and Michael Stipe can go real time to their fanbase, but on the hip-hop side of things, I only know that Manhattan clam chowder is the special ingredient to Q-Tip’s spaghetti recipe? I wanted to change all that.

Shawn Gee: Me and Ahmir sat down and said we want to build a Roots website. Back then there was no real business plan. It was more of an advertisement for the albums and shows. We wanted to go after TheRoots.com, which was the obvious name for the site, but a fan had already taken it and built a fanpage.

Questlove: I’d never even bothered to see if there was anything about The Roots online. One day, I searched and saw that someone had put up a Roots fan page—real primitive graphics and stuff. I actually got involved in that board, trying to answer questions, and I kind of got my feet wet giving updates and things like that on this website.

Shawn Gee: We started the negotiation with that fan and from the very beginning they were interested in selling it. But we saw early on that it was going to be a long, drawn-out process—the lawyers were going to have to get involved and everything.

Dan Petruzzi: They had been putting the Okayplayer logo on albums for years. It was really Quest’s desire to have a platform to promote his music and the band’s music and also to connect with fans of the Roots and fans of music, cause he’s a super true music head, and he knows that people who are fans of the Roots are also really into music.

Shawn Gee: Ahmir came up with the name Okayplayer. It was sort of a brand without a concept. He liked to design the covers in classic Blue Note style. And if you look at all the early albums prior to Things Fall Apart—Illadelph Halflife, Philly Organics—there was this logo that said Okayplayer: Giving You True Notes Since 1987. Long story short, Ahmir decided: Why don’t we name our website Okayplayer.com?

Here in Philly there was a colloquialism where people said, “OK, player!” as in, “Alright, dude.” But I’m not sure if that’s where Ahmir got it from. Ironically, we were able to get TheRoots.com later on down the line, but we'd already built this Okayplayer brand.

Questlove: [The name came from] Tramp. He was an art director. Back in the days of The Source, he did a cartoon called “A View From The Underground,” back in like ’91, ’92. And he designed some of our first few album covers. He did our EP From the Ground Up, he did Do You Want More?!!!??! and he also did Illadelph Halflife.

For The Ground Up, Tramp didn’t have the logo. So he just made up the first thing that came to his head until he got the proper fonts and logos from Geffen. When he showed me the first draft of the design, he just wrote “Okayplayer” in a box. And I thought OK, that’s the most Blue Note–looking artwork font-wise and everything. So then when he turns in the proper artwork with the label stuff and everything, I didn’t like it. It lost its Blue Note appeal. I told him, put that “Okayplayer” back on and just stick the logo on the back of the record. It didn’t make sense at the time, but it just felt like it needed to be there. It wasn’t like it was a label or anything, I just wanted Okayplayer to be there. And then it literally just stuck and somehow it’s found itself onto all 15 of our records.

Its meaning of course is slang for, “Well alright,” that type of thing. We didn’t say it as much as people would have thought. It was a temporary mistake that I actually liked the visual of, and we just kept it.